5710
T. Ankner, G. Hilmersson / Tetrahedron Letters 48 (2007) 5707–5710
´
7. (a) Namy, J. L.; Girard, P.; Kagan, H. Nouv. J. Chim.
18. Dahlen, A.; Hilmersson, G. Tetrahedron Lett. 2003, 44,
1977, 1, 5; (b) Girard, P.; Namy, J-L.; Kagan, HB. J. Am.
Chem. Soc. 1980, 102, 2693.
2661.
19. Davis, T. A.; Chopade, P. R.; Hilmersson, G.; Flowers,
R. A. II. Org. Lett. 2005, 7, 119.
20. Kim, M.; Dahlen, A.; Hilmersson, G.; Knettle, B. W.;
8. (a) Namy, J. L.; Souppe, J.; Kagan, H. B. Tetrahedron
Lett. 1983, 24, 765; (b) Molander, G. A. In Renand, P.,
Sibi, M. P., Eds.; Radicals in Organic Synthesis; Wiley-
VCH: Weinheim, 2001; Vol. 1, pp 153–182; (c) Krief, A.;
Laval, A.-M. Chem. Rev. 1999, 99, 745; (d) Molander, G.
A. Chem. Rev. 1992, 92, 29; (e) Molander, G. A.; Harris,
C. R. Chem. Rev. 1996, 96, 307; (f) Taniguchi, N.;
Uemura, M. J. Am. Chem. Soc. 2000, 122, 8301; (g)
´
Flowers, R. A., II. Tetrahedron 2003, 59, 10397.
´
21. Dahlen, A.; Sundgren, A.; Lahmann, M.; Oscarson, S.;
Hilmersson, G. Org. Lett. 2003, 4085.
´
22. Dahlen, A.; Petersson, A.; Hilmersson, G. Org. Biomol.
Chem. 2003, 1, 2423.
23. (a) Henry, L. Acad. Sci. Ser. C 1895, 120, 1265; (b) Henry,
L. Bull. Soc. Chim. Fr. 1895, 13, 999.
Furstner, A.; Csuk, R.; Rohrer, C.; Weidmann, H. J.
¨
Chem. Soc., Perkin Trans. 1 1988, 1729; (h) Steel, P. G. J.
Chem. Soc., Perkin Trans. 1 2001, 2727; (i) Hasegawa, E.;
Curran, D. P. Tetrahedron Lett. 1993, 34, 1717; (j) Rivkin,
A.; Nagashima, T.; Curran, D. P. Org. Lett. 2003, 5, 419;
(k) Molander, G. A.; Brown, G. A.; de Garcia, I. S. J. Org.
Chem. 2002, 67, 3459.
24. Representative procedure for the reduction of aliphatic
nitro compounds to amines: To a stirred solution of SmI2
(0.1 M, 20 ml, 2.0 mmol, 6 equiv) in THF under a nitrogen
atmosphere,
isopropylamine
(4.0 mmol,
0.342 ml,
12 equiv) and water (20 mmol, 0.36 ml, 60 equiv) were
added followed by dropwise addition of the nitro com-
pound dissolved in THF (0.33 mmol, 3.3 ml, 0.1 M,
1 equiv). After the addition the reaction was quenched
with diethyl ether (20 ml). The reaction mixture was treated
with a solution of potassium carbonate and sodium
potassium tartrate in water (10% w/v, 20 ml). The aqueous
phase was extracted with diethyl ether (2 · 10 ml). The
combined organic extracts were dried and concentrated to
afford the amines as colourless oils or crystals.
9. Zhang, Y.; Lin, R. Synth. Commun. 1987, 27, 329.
10. Banik, B. K.; Mukhopadhyay, C.; Venkatraman, M. S.;
Becker, F. F. Tetrahedron Lett. 1998, 39, 7243.
11. Kende, A. S.; Mendoza, J. S. Tetrahedron Lett. 1991, 32,
1699.
12. Yacovan, A.; Hoz, S. J. Org. Chem. 1997, 62, 771.
13. Chengzhi, Y.; Liu, B.; Hu, L. J. Org. Chem. 2001, 66,
919.
14. Brady, E. D.; Clark, D. L.; Keogh, W.; Scott, B. L.;
Watkin, J. G. J. Am. Chem. Soc. 2002, 124, 7007.
25. The workup used in the reduction of unsaturated nitro
compounds was slightly modified and employed acidic
workup of the post reaction mixture with 1 M HCl. This
was washed once with dichloromethane before treatment
with a saturated solution of sodium potassium tartrate
and basification with KOH. Repeated extraction of the
aqueous phase with dichloromethane yielded the amine in
the yields specified in Table 2.
´
15. Dahlen, A.; Hilmersson, G. Tetrahedron Lett. 2002, 43,
7197.
´
16. (a) Dahlen, A.; Hilmersson, G.; Knettle, B. W.; Flowers,
´
R. A., II. J. Org. Chem. 2003, 68, 4870; (b) Dahlen, A.;
Hilmersson, G. J. Am. Chem. Soc. 2005, 127, 8340.
´
17. Dahlen, A.; Hilmersson, G. Chem. Eur. J. 2003, 9, 1123.